Chuck Siu is an enterprise product and AI transformation executive with deep expertise leading large-scale organizational change across product, IT, security, platform operations, and AI enablement. Currently Vice President of Product Management for Enterprise Journey & AI Transformation at Gap Inc., he focuses on helping large organizations operationalize AI at scale while bridging the gap between frontier AI innovation and enterprise execution reality. With leadership experience spanning Fortune 1000 environments across retail, enterprise SaaS, cybersecurity, and corporate technology, Chuck is known for driving human-centered AI transformation programs that move organizations from experimentation to sustained adoption. Prior to Gap Inc., he led enterprise AI transformation and global IT operations at Anaplan, overseeing AI strategy, governance, literacy, and rollout initiatives across a 100+ application enterprise ecosystem supporting teams worldwide. Chuck’s work combines deep operational execution with a strong focus on organizational behavior, change management, and AI adoption frameworks. He has become widely recognized for translating emerging AI capabilities into practical enterprise workflows, helping teams achieve significant efficiency gains through AI-assisted research, product development, service management, and operational transformation.